Thiochroman → 6-[3-(1-Acetylpiperidin-4-yl)-1-oxopropyl]-3,4-dihydro-2H-1-benzothiopyran

HRID 327401

반응식

HRID 327401 반응식
[S:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][CH2:2]1.[C:11]([N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][C:22](Cl)=[O:23])[CH2:16][CH2:15]1)(=[O:13])[CH3:12].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[C:11]([N:14]1[CH2:15][CH2:16][CH:17]([CH2:20][CH2:21][C:22]([C:9]2[CH:8]=[CH:7][C:6]3[S:1][CH2:2][CH2:3][CH2:4][C:5]=3[CH:10]=2)=[O:23])[CH2:18][CH2:19]1)(=[O:13])[CH3:12]

참가 물질

5

반응물 3

HCID 137415ThiochromanHCID 6451240Aluminum(III) ChlorideHCID 104659513-(1-Acetyl-4-piperidinyl)propionyl chloride

생성물 1

HCID 191084806-[3-(1-Acetylpiperidin-4-yl)-1-oxopropyl]-3,4-dihydro-2H-1-benzothiopyran수율 81.6%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a mixture of 3,4-dihydro-2H-1-benzothiopyran (1.5 g) and 3-(1-acetylpiperidin-4-yl)propionyl chloride (2.18 g) in 1,2-dichloroethane (20ml) was added aluminum chloride (3.2 g) portionwise at 10°-15° C. The mixture was stirred at room temperature for 2 hours then refluxed for additional 2 hours, and poured into icewater. The mixture was extracted with dichloromethane, washed with water, dried over anhydrous sodium sulfate. The solvent was distilled off. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate) to obtain 2.7 g of the title compound as a pale yellow oil.

후처리

  1. temperaturethen refluxed for additional 2 hours
  2. additionpoured into icewater
  3. extractionThe mixture was extracted with dichloromethane
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customThe residue was purified by silica gel column chromatography (developing solvent: ethyl acetate)

출처 및 근거

ORD 기록
ord-fcb979243cbd468aaea38beb0bf9cc98
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05273974

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